Arora Sahil, Sneddon Dorian S, Hoye Thomas R
Department of Chemistry, University of Minnesota, 207 Pleasant St. SE, Minneapolis, MN 55455 USA.
European J Org Chem. 2020 May 3;2020(16):2379-2383. doi: 10.1002/ejoc.201901855. Epub 2020 Feb 13.
-Benzynes can be utilized to construct heterocyclic motifs using various nucleophilic and cycloaddition trapping reactions. Acridines have been synthesized by capture of -diarylimines with benzynes generated by classical methods (i.e., from -elimination of precursor arene compounds), although in poor yields. We report here that these imines can be trapped by benzynes generated by the hexadehydro-Diels-Alder (HDDA) reaction in an efficient manner to produce 1,4-dihydroacridine products. These dihydroacridines were subsequently aromatized using MnO to provide structurally complex acridines.
苯炔可通过各种亲核反应和环加成捕获反应用于构建杂环基序。虽然产率较低，但通过经典方法（即从前体芳烃化合物的β-消除）生成的苯炔捕获二芳基胺已合成了吖啶。我们在此报告，这些亚胺可以被十六脱氢狄尔斯-阿尔德（HDDA）反应高效生成的苯炔捕获，以产生1,4-二氢吖啶产物。这些二氢吖啶随后用MnO芳构化，以提供结构复杂的吖啶。
